Flavoring substances and their preparation

ABSTRACT

Process for the preparation of flavors of onion and bacon which comprises reacting certain sulfide or hydrosulfide sulfur compounds with certain aldehydes and the products produced thereby.

United States Patent Wiener [451 Mar. 21, 1972 [54] FLAVORING SUBSTANCESAND THEIR PREPARATION [72] Inventor: Charles Wiener, Middletown, NY.

[73] Assignee: Polaks Frutal Works Inc., Middletown,

[22] Filed: Aug. 1, 1968 211 App]. No.: 749,271

[30] Foreign Application Priority Data Aug. 15, 1967 Great Britain..37,445/67 11.8. CI. ..99/l40 R ..A23l 1/26 Field of Search, ..99/ l 40T. Moeller, Inorganic Chemistry, 515- 516, John Wiley and Sons, NewYork, 1953.

PrimaryExaminer-Morris O. Wolk Assistant Examiner-SidneyMarantzAttorney-Morgan, Finnegan, Durham & Pine [5 7] ABSTRACT Process for thepreparation of flavors of onion and bacon which comprises reactingcertain sulfide or hydrosulfide sulfur compounds with certain aldehydesand the products produced thereby.

8 Claims, No Drawings respect to this process in that it is carried outin alkaline media without the use of triethyl citrate. The quality andstrength of the resulting products are superior. Also, acetaldehyde whenreacted via the process described in the present invention gives anonion flavor rather than a sauerkraut odor as was reported in earlierwork (U.S. Pat. No. 2,594,379).

The process of this invention comprises reacting a sulfur compoundselected from the group consisting of ammonium sulfide, ammoniumhydrosulfide, alkali metal sulfides, alkali metal hydrosulfides,alkaline earth metal sulfides, alkaline earth metal hydrosulfides andamino hydrosulfides with (l) an aldehyde selected from the groupconsisting of 3-methyl butyraldehyde and Z-methyl butyraldehyde to forma product having a bacon-like flavor, or (2) an aldehyde selected fromthe group consisting of acetaldehyde and propionaldehyde to form aproduct having an onion-like flavor.

Examples of alkali metal sulfides and hydrosulfides that may be used aresodium sulfide, potassium sulfide, sodium hydrosulfide and potassiumhydrosulfide. Examples of alkaline earth metal sulfides andhydrosulfides are calcium sulfide and calcium hydrosulfide. An exampleof an amine hydrosulfide is 2-amino ethanol hydrosulfide.

It has been found that the flavor quality is improved if the resultingreaction mixture is acidified to a pH in the range of l to 6 with asuitable acidifying agent (e.g., hydrochloric acid, sulfuric acid, etc.)

Factors which may affect the quality of the flavors produced include thenature and relative amounts of the aldehydes and sulfur reagents used,the amount of solvent used, and the time and temperature at which thereaction is performed.

When a solvent is used in the reaction this is usually water, glycerolor propylene glycol. The amount of any ofthese alone or in combinationused in the reaction should be at least l percent; generally l0-30percent is used based on the total weight ofthe sulfur reagent andaldehyde. Amounts of solvent of up to 5,000 times the total weight ofthe aldehyde plus the sulfur reagent can, however, also be used.

The reaction may be carried out at temperatures from between 0 and 200C., usually reaction times of from 1 minute to 4 hours are used.

To obtain flavors of high quality from 0.1 mole to 10 moles ofaldehydeare used per 1 mole of sulfur reagent.

Onion and bacon flavors according to this invention may be incorporatedin a wide variety of products such as vegetable oils, salad dressings,cheeses. soups, crackers, etc., where either onion or bacon flavors aredesired.

EXAMPLE I The following were mixed together and warmed at 6070 C. for 5minutes:

l g. sodium hydrosulfide l g. acetaldehyde 20 ml. water The mixture wascooled and acidified with concentrated HCl to pH 1 and allowed to standuncovered 1 hour at room temperature to dispel excess hydrogen sulfide.The resulting material had a boiled onion aroma.

EXAMPLE 2 The following material was saturated with hydrogen sulfide:

10 g. 2-amino ethanol to this was added in portions and maintaining thereaction temperature between 7080 C.

6 g. propionaldehyde.

The mixture was stirred for 0.5 hours. This material has an onion-likeodor. The mixture was then oured into ml. of water and acidified to pH 1and allowe to stand uncovered at room temperature to dispel excesshydrogen sulfide. The material thus obtained had a strong fresh onionaroma.

EXAMPLE 3 The. following materials were mixed together and boiled for 5minutes:

1 g. sodium sulfide 1 g. propionaldehyde 10 ml. water After thereactionperiod the material was acidified to pH 1 with concentratedhydrochloric acid and allowed to stand uncovered for l hour to dispelexcess hydrogen sulfide. A product having an onion aroma was thusobtained.

EXAMPLE 4 The following materials were mixed together and heated at70-8O C. for 5 minutes:

1 g. 2-aminoethanol hydrosulfide 0.4 g. isovaleraldehyde The materialhad bacon-like qualities. The mixture was then poured into water andacidified to pH 3 with concentrated hydrochloric acid and allowed tostand uncovered for 1 hour to dispel excess hydrogensulfide giving astrong crisp baconlike product.

What is claimed is:

l. A process for the preparation of a food flavor comprising reacting asulfur compound selected from the group consisting of ammonium sulfide,ammonium hydrosulfide, alkali metal hydrosulfides, alkaline earth metalsulfides, alkaline earth metal hydrosulfides and amino hydrosulfideswith an aldehyde selected from the group consisting of 3 -methylbutyraldehyde and Z-methyl butyraldehyde at a temperature between 0 and200 C. wherein the mole ratio of aldehyde to sulfur compound is0.l:l-l0:l to form a product having a bacon-like flavor, said processbeing carried out in the absence of an aliphatic ester of a hydroxypolybasic acid.

2. A process according to claim I wherein the reaction mixture isacidified.

3. A food component prepared in accordance with claim I.

4. The method of imparting bacon-like flavor to a foodstuff comprisingtreating the foodstuff with the product of claim 3.

5. A process for the preparation ofa food flavor comprising reacting asulfur compound selected from the group consisting of ammonium sulfide,ammonium hydrosulfide, alkali metal hydrosulfides, alkaline earth metalsulfides, alkaline earth metal hydrosulfides and amino hydrosulfideswith an aldehyde selected from the group consisting of acetaldehyde andpropionaldehyde at a temperature between 0 and 200 C. wherein the moleratio of aldehyde to sulfur compound is 0. l l-lOzl to form a producthaving an onion-like flavor, said process being carried out in theabsence of an aliphatic ester of a hydroxy polybasic acid.

6. A process according to claim 5 wherein the reaction mixture isacidified.

7. A food component prepared in accordance with claim 5.

8. The method of imparting onion-like flavor to a foodstuff comprisingtreating the foodstuff with the product of claim 7.

@2 3 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION ?atem: No.3,650,771 I Dated March 21, 1972 Inventofli) Charles Wiener It 15certified that; error appears in the above-identified patent and thatsaid Letters Patent are hereby corrected as shown below:

Column 2', line 6, change "has" to --had-- Column 2, line 26, Chang "80C. to --80C.--.

Signed and sealed this 15th day of August 1972.

(SEAL) Attest:

ROBERT GOTTSCHALK Commissioner of Patents EDWARD M.FLETCHER,JR.Attesting Officer

2. A process according to claim 1 wherein the reaction mixture isacidified.
 3. A food component prepared in accordance with claim
 1. 4.The method of imparting bacon-like flavor to a foodstuff comprisingtreating the foodstuff with the product of claim
 3. 5. A process for thepreparation of a food flavor comprising reacting a sulfur compoundselected from the group consisting of ammonium sulfide, ammoniumhydrosulfide, alkali metal hydrosulfides, alkaline earth metal sulfides,alkaline earth metal hydrosulfides and amino hydrosulfides with analdehyde selected from the group consisting of acetaldehyde andpropionaldehyde at a temperature between 0* and 200* C. wherein the moleratio of aldehyde to sulfur compound is 0.1:1-10:1 to form a producthaving an onion-like flavor, said process being carried out in theabsence of an aliphatic ester of a hydroxy polybasic acid.
 6. A processaccording to claim 5 wherein the reaction mixture is acidified.
 7. Afood component prepared in accordance with claim
 5. 8. The method ofimparting onion-like flavor to a foodstuff comprising treating thefoodstuff with the product of claim 7.